


A few of Dean Winchester's favorite things

by BennedictCucumber



Category: Supernatural, destiel - Fandom
Genre: AU, Alternate Universe, Angst, Coffeeshop AU, Fluff, Heartbreak, M/M, Pining, Smut
Language: English
Status: In-Progress
Published: 2013-06-24
Updated: 2013-08-07
Packaged: 2017-12-16 01:55:42
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 5,258
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/856451
Author URL: https://archiveofourown.org/users/BennedictCucumber/pseuds/BennedictCucumber
Summary: <blockquote class="userstuff">
              <p>Dean Winchester loved his job. He worked at Supernatural (Dean was pretty positive that his boss, Bobby, named the place while under the influence of some sort of exotic alcohol, or had lost a bet) and was the only male barista there who could memorize orders without the use of paper and pen, hence his superiority over everyone and one of the many reasons he loved his job.</p><p>But the main reason he loved his job was because of a man who looked way too good at 9 pm, with snow covered hair and blue eyes that Dean swore were contacts.</p>
            </blockquote>





	1. Cappuccino almost sounds like Castiel

**Author's Note:**

> Dean is pining and Castiel just wants a drink.

Dean Winchester loved his job. He worked at Supernatural (Dean was pretty positive that his boss, Bobby, named the place while under the influence of some sort of exotic alcohol, or lost a bet) and was the only male barista there who could memorize orders without the use of paper and pen, hence his superiority over everyone and one of the main reasons he actually comes to work every day.

A few of the other reasons usually came by in high heels and scoop-neck shirts, smearing lipstick onto their Styrofoam cups and brushing his hand too much to be an accident. He was fawned over by college girls (due to the location of Amherst College only a few blocks from the shop) and his tips were something to gloat about. The customers were relatively polite, as most of them came in before or after work, usually half asleep and too tired to give a damn when he (accidentally, of course) charged them a little extra for their drinks. Hell, with his work hours, Dean was more tired than most of the patrons who stopped in for their morning coffee and cakes, so they should be grateful he doesn’t price everything at $50.

“Double expresso, light cream, two sugars, hold the milk, stirred twice.” “Turbo express coffee, 4 sugars, half a shot of cream, an two shots of caramel flavoring, not mixed.” “ Ice tea, no sugar (or sweeteners), and three seedless lemons floating at the top.” These were a few of the things that made Dean Winchester hate his job.

Granted, these orders were seldom given to him, due to his usual tendency of mocking the customer ordering and proceeding to throw a fit when they threw the drink back at him (literally speaking, he had had a good share of drinks tossed onto his green apron). But, when Bobby was hung-over, or just starting to get drunk, Dean was given the orders from whom he deemed the “bratty hipster” crowd. They came in at odd hours (Like at 10, around closing time, or 4 in the morning, when he was just arriving at the homely brick building wedged in between a florist’s shop and a streetlight.

But now, Dean had one more reason to add to his list of reasons why he loved his job. This reason came waltzing in on a brisk Monday morning, snow peppering his navy colored wool coat and dusting his mussed I-just-woke-up-but-I -still-look-perfect (a style Dean had been working on perfecting for years) dark hair. His cheeks were pink, as well as was his nose, and the way his clear blue eyes widened when he entered the shop, looking around as if he had stumbled into Narnia instead of a coffee shop, Dean would be lying if he said he wasn’t blushing.

The man confidently strode up to the counter, his hands pulling off warm winter gloves and stuffing them in his pocket, revealing hands that looked too soft to have been natural. He gently drummed his nails on the granite countertop, his eyes scanning the chalk board hanging over Dean’s head reading SPECIALS.

Dean only had a few seconds to admire the man’s features- and Dean used those few seconds very well. His eyes scraped over his angled jawline, his protruding Adam’s apple, the way his eyelashes looked way too long to be real, and the way he shifted from foot to foot as he read both chalkboards with the intensity of a professional chess player.

“Do you still serve cappuccino?” Dean snapped his gaze away from the small look of the man’s taut chest that was peeking out from the open buttons of his coat and forced his eyes to stop doing that thing where he looks like he wants to fuck someone. The man’s eyes were much too blue for Dean’s comfort, and he immediately forgot his response when he heard the gruff tones of the man’s voice, the voice of a 2 pack-daily smoker, and one of a prepubescent teenage boy.

“Yes,” Dean finally forced his vocal chords to form sound and his mouth to form words long enough to answer the man’s question, “Wet or dry?” Dean cursed in his head as the man’s tongue gently swiped across his bottom lip long enough for Dean’s pants to get tighter.

“Dry, and soy milk, please. Size medium.” Dean nodded, once again rendered mute as he man pulled out his wallet from his back pocket, giving Dean the perfect sight of his perky ass. He swiped his card like an expert, signing the screen with the little cheap pen attached, and although Dean wouldn’t admit it, he looked down long enough to see the man meticulously scrawl out Castiel Novak.

Dean stumbled away from the counter and began preparing the drink. He pressed buttons, pulled levers, and spent way too much time deciding if he should scribble his number across the surface of the cream-colored Styrofoam cup emblazed with the Supernatural Coffeehouse logo. He opted for no, because if Castiel’s sultry looks and prolonged touching were a sign of friendship and not one for I want to get in your pants, things could get awkward very quickly.  
Dean finished the drink with more care than he gave to other customers, making sure the foam didn’t tint the edging on the cup, and weighing it in his hands to assess his work. 

The whole ordeal took him a good 8 minutes, and the baby-faced probably-older-than-Dean but-still-extremely-sexy customer switched his seat from teetering across the edge of Dean’s counter to a stool table by the window.

“Medium cappuccino! Dry, soy milk!” Dean called out, his voice softer than usual, and Castiel stood up, waltzing over and taking it from Dean’s sweaty hand. A few other patrons turned their heads, those who weren’t engrossed by their cell phones and laptops, before sighing and shifting away, discouraged that their order wasn’t ready.

“Thank you, Dean.” His smile was genuine and blinding white, and Dean only blinked and finally managed to stutter out a you’re welcome before the man walked off with a handful of napkins and a coffee cup that, sadly, didn’t have Dean’s number on it.

And that’s when Castiel Novak became his number one reason he loved his job.


	2. A list of things that would look cute on Dean Winchester's butt

**Summary for the Chapter:**

> Dean didn’t want to admit it, but he waited the rest of the week for Castiel. Hell, he would’ve stayed working at Supernatural for the rest of his god damn life (not to say that he didn’t, but that’s not of importance) if it meant he may have a chance to see Castiel, and his eyes that looked like the blue of a cool snow cone, and his perky butt, both of which Dean swore were not natural.

**Notes for the Chapter:**

> Dean makes an ass out of himself whilst around attractive men (usually ones with blue eyes, insanely raspy voices, and incredibly tight jeans).

Dean didn’t want to admit it, but he waited the rest of the week for Castiel. Hell, he would’ve stayed working at Supernatural for the rest of his god damn life (not to say that he didn’t, but that’s not of importance) if it meant he may have a chance to see Castiel, and his eyes that looked like the blue of a cool snow cone, and his perky butt, both of which Dean swore were not natural.

Every time the chimes sang throughout the shop, or when the door creaked open in the cold winter winds, Dean dropped what he was doing and practically army-crawled over the countertop just to see if the raven haired man was standing between the outside world and Dean’s one of coffee scented skin and lip-gloss smeared tips. And each time, Dean was disappointed, and would awkwardly go back to what he was doing, ignoring the patrons who had just witnessed his embarrassment and him spilling their coffees.

After four days, (Dean could definitely not tell you how many hours it had been, that would be ridiculous!) while Dean was working on making an elderly woman her fourth cup of “irish” coffee (well, Dean made the coffee, she added the liquor and gave him some as well) the bells attached to the door chimed and Dean still held out enough hope that it was Castiel to look up towards the noise. For once, he was not mistaken, and standing there was all 6 feet of him, still wrapped in a wool coat, but this time with a scarf wrapped gracefully around his slender neck (Dean knew he was obsessed when he used the word graceful to describe Castiel in a later fashion). He shook out his hair, mussing through it with glove-covered hands, and then waltzed up to the counter, this time looking Dean directly in the eyes instead of trying to interrogate the creaking chalkboards above his strawberry-blonde tufts of hair.

“Could I try a…..Caramel Macchiato?” Castiel’s eyes were gone again, his focus instead on trying to extract his wallet from his form-fitting jeans that men like him should seriously not be allowed to wear.

“Yes?” His reply was more of a question, and Castiel smiled softly, his fingers fumbling through his wallet as he searched for a credit card.

“Then I will have a caramel macchiato, Dean.” Dean fluttered his eyelids slightly, in an attempt to be flirty (unintentionally, of course) and to clear his vision as Castiel stared back at him, his tongue doing that thing that made Dean feel it on his skin. Castiel chuckled (Chuckled, more like giggled) and Dean finally nodded. Grown men should not be allowed to act as adorable as he was now.

Do you want…,” an awkward cough placed into the middle of Dean’s sentence interrupted him, “do you want anything to eat with that?” Castiel’s eyes were on Dean again, and the piercing blue of them (seriously, how the fuck were they that blue) made Dean a bit twitchy but made Castiel a lot more attractive. Castiel chuckled (Giggled? Chuckled? Honestly this man didn’t have a separate sound for the two) and he strummed his fingers on the granite countertop, his fingers only millimeters away from Dean’s own (they were quite a bit sweaty, which was not at all attractive) and began rereading the chalkboard of specials above Dean’s head.

“What do you recommend, Dean?” Oh god, if only Castiel knew what Dean would recommend to him if they weren’t within earshot of almost a dozen different teenagers and elderly men. Me, you, dinner, then back to my place where I can fu-

“The cupcakes are really nice. My brother, Sammy, baked them earlier this morning when he was here. My favorite’s chocolate, but if you’re not into chocolate the pumpkin spice ones are really tasty, or the oreo cheesecake. Working here is pretty much the whole reason I can’t lost 10 pounds.” Dean sighed internally, gracious to his conscious that he didn’t finish his earlier sentence out loud, even though he was mentally slapping himself for admitting to a very attractive man that he couldn’t lose 10 pounds. It wasn’t as if he was flabby or anything; he just had a thing for sweets!

"Well, I have to be back at work in 20,” Castiel paused, staring at his watch as if he was debating with it if that was the correct time, “So I’ll get some to bring back. A dozen, I guess? That should be enough?”

“Alright. Any specific flavors?” Dean slid the glass casing away from the display case full of sweets and pulled out a tray of assorted cupcakes, ranging from Pink Daiquiri to Chocolate Lover’s Delight.

“Um… Well, I’ll get one of the oreo cheesecake, seeing as how I could probably stand to gain 10 pounds,” Castiel chuckled, and Dean was positive Castiel could feel the heat radiating from his cheeks, “And, a um… Hot Chocolate, that sounds good. Two Funfetti, seeing as how my co-workers are practically 6 years old… Oh, a Strawberry Shortcake sounds nice. Pumpkin spice would be good too… And, I don’t really care about the rest, put in whichever ones you like.” Castiel smiled up at Dean, and Dean swore his heart stopped beating for most of the time Castiel smiled; and even though it sound juvenile (I mean, come on, this isn’t some Nicholas Sparks romance novel) Dean actually thought he had had a heart attack.

“Right…. I’ll wrap these and…. Chuck will get your drink.” Castiel nodded, running his fingers along the edges of his credit card and examining it with the intensity of an art critic studying Van Gough’s work (or trying to piece together the reason why he cut off his ear, which always had had Dean stumped) before handing it to Dean. Dean, because he has the grace of a newborn giraffe with only one leg, managed to drop the card, and, of course, the cupcake he was holding.

“Shi- Sorry. I’m sorry, man. I’ll get you a new one…” He scrambled off, chucking the card onto the counter while, simultaneously, grabbing a fresh cupcake for Castiel, who was laughing like a mental.

“What’s so funny, pretty boy? Haven’t you ever dropped something before?” Dean cursed in his head; “pretty boy”? Seriously?

“I did not mean to offend, Dean, but,” He giggled again, stifling his chuckles behind his hand before continuing (GROWN MEN CANNOT GIGGLE! SERIOUSLY, WHAT IS UP WITH THIS MAN-CHILD-SEXUALLY-ATTRACTIVE-BLUE-EYED-GUY!), “you’ve gotten frosting on your butt.”

Cue Dean turning around and finding a smear of hot pink frosting on his butt (which, in the defense of saving Dean's manliness, and sexual attractiveness, was looking very perky that day) and a giggling group of barista's who Dean would make sure were fired for incompetence and disobeying uniform/ "dress code" (which, for once, Dean minded).

And thankfully, before Dean could make an ass out of himself in front of Sexy-Man-Child anymore, Chuck came over and handed him his drink which, sadly, did not have Dean’s number on it, and Castiel grabbed his cupcakes with a smile that was worth having to spend $8 on dry-cleaning for his jeans.

**Notes for the Chapter:**

> Hey guys! Hope you enjoy the fic! Please leave comments and kudos to let me know. I'll be updating every week on Tuesdays! Also, if you have any suggestions/ constructive criticism, please leave it in the form of a comment; i am open to any and all suggestions!


	3. The adventures of Moose-boy and his brother, Dean

**Summary for the Chapter:**

> “Sammy!” Dean kicked open the door to his shared apartment- the one he shared with Moose, a.k.a his brother Sam- and made just enough noise to wake his younger brother from his nap he was taking on the kitchen counter. Sam was “comfortably” hunched over a stack of books the thickness of Dean’s ego, with papers sticking out haphazardly around him, his mouth opened just enough for a small amount of spittle to leak out. “I’ve got dinner!”  
> “Wha-!” Sam bolted upright in his seat with enough force that he managed to rocket himself backwards, slamming his chair onto the kitchen floor, “Dinner?”  
> That’s Sam alright, Dean thought, Always excited by food.

**Notes for the Chapter:**

> Dean almost throws up on the floor over sexy snowcone-eyes, and ends up waiting outside of a lecture hall in sub-zero temperatures, catching slight glimpses of a mop of brown hair and someone's very perky butt.

Dean, most certainly, did not have a huge, overwhelming crush, on Castiel. He definitely did not think about him on the way home from work, on the way to work, or on the way to pick Sam up. And he definitely did not think about him in bed. And even more definitely, he did not think of Castiel's beautiful eyes that made him want to get down on one knee and serenade the man like those fancy Italian men do in operas (Usually to women, but that is not important).

I just think he’s nice lookin’, Dean thought, as an attempt to salvage what was left of his manliness as he walked up the millions of flights of stairs to his apartment, because his roommate insisted that the top floor had a much nicer view that the bottom (Dean thinks that secretly, he was just trying to get Dean to lose weight).

“Sammy!” Dean kicked open the door to his shared apartment- the one he shared with Moose, a.k.a his brother Sam- and made just enough noise to wake his younger brother from his nap he was taking on the kitchen counter. Sam was “comfortably” hunched over a stack of books the thickness of Dean’s ego, with papers sticking out haphazardly around him, his mouth opened just enough for a small amount of spittle to leak out. “I’ve got dinner!”

“Wha-!” Sam bolted upright in his seat with enough force that he managed to rocket himself backwards, slamming his chair onto the kitchen floor, “Dinner?”  
That’s Sam alright, Dean thought, Always excited by food.

“I got take-out on the way home for my widdle brother who’s been studying so damn hard!” Dean grinned, slamming the box of food onto the table and opening the contents, hamburgers and golden French fries pouring out of the limp paper bag it all came in.

“I am studying hard, Dean.” Sam grumbled, getting up off of the cold floor and fixing the chair which was, surprisingly, not broken by Sam’s large physique. He reached one hand out, snatching a fry from Dean’s frosting-stained hand, and shoved it in his mouth with the largest shit-eating grin Dean had ever seen. “I don’t just bake cupcakes all day, like some people.”

“Watch it, Moose-boy, those cupcakes pay the rent and heating bill, so be thankful. Not everyone can be super-lawyers like you; the world needs more cupcakes anyways.” And with that, Dean grabbed his burger, knocked his younger brother on the back of his head (which acted like a current to swish his expensive, and “completely necessary”, haircut into his face.) and walked to the living room, trying to calculate the amount of time it would take Sam to fix his hair to his liking (or make it look the same exact way it had before).  
“I’m kidding Dean, you know I love your coffee and little girly-ass cupcakes.” Sam chuckled, rustling his hair back into place with the hand that wasn’t focused on shoving his burger into his mouth, ketchup and other unknown condiments staining his shirt.

“You only like ‘em cause you get free samples.” Dean huffed good-naturedly; inspecting his burger as he waited for the TV to play something other than shitty reality shows.  
“Liar!” He exclaimed, coughing and hacking onto the table as he choked on parts of his burger, Dean watching him the whole time and thinking Karma, Moose-boy.  
“What are you studying for anyways? Something today?” Dean hopped off of the couch and waltzed over to Sam, grabbing a notebook out of his hand and inspecting the contents. There were illegible scribbles covering the entirety of it (Sam’s attempt at writing actual words), and a lot of highlighted things that Dean could barely make out. As Sam was in school to become a lawyer, Dean tried to make a point of interesting himself in whatever Sam was learning about, even though he didn’t actually give a shit about any of it. But, Sam did enjoy Dean’s attempts at understanding lawyer-isms, which always made for a good laugh if he had had any beers in him, and as Dean was helping his little brother pay for college (along with money their father had left them when he died) it was only polite to allow Dean a small glimpse into the world of someone with a college degree.

Of course, Sam didn't just go to school. No, he also worked a shift as a part-time fitness instructor down at the local gym, and he interned at a law-firm in the next town over on weekends. Sam was pulling less than half of his weight in bills and rent, while Dean was pulling three Dean's worth of it. But Dean wasn't bitter about this, no sir-ee. He knows Sam would pay more if their were more hours in a day, and when he gets chosen to work at the law firm he will reimburse Dean with all of the money he owes him (Which Dean has, unconvincingly assured him would not be necessary). All in all, the situation worked out better than both brothers had expected, and Dean gets free baked goods, so that's always a plus for living with your younger, taller, and much smarter brother.

“Yeah, my professor for Physiology assigned our final on the same day as my final for Political Science, which is tomorrow night before Thanksgiving break. It was a total douche move, but the guy’s alright so I’ll deal with it.” As Sam spoke, bits of crumbs spewed out of his mouth and landed on his papers, making Dean grumble with maternal insticts and toss him a napkin (that was, hopefully, not too dirty, as laundry day wasn’t for another few weeks, when Dean would finally be paid, as Bobby had gone on another drinking binge and forgotten that he owns a coffee house, the 'idjit).

“What’s the guy’s name? I could beat him up, seeing as how I’m so strong and masculine.” Sam snorted at that (as he was noticeably taller and buffer than Dean was) and threw his head back in a cackle.

“Mr. Novak. And no Dean, he knows jujitsu, so you’d probably get your ass handed to you on a platter.” Dean huffed at Sam’s remark, crossing his arms like an indignant child, before running over and stealing a handful of Sam’s fries.

Then it finally registered in Dean’s mind; Castiel Novak, a.k.a adorably-sexy-baby-man-child with blue snow cone eyes (who can apparently do jujitsu, which Dean considered a major turn-on). His eyes widened, and he almost spit out his fries if he hadn’t regained control of himself and, also, remember that the floors would not be washed until they bought a mop of some sort, and it would not look good to guests if there were French-fry pukes stains on the floor.

And that is the story of how Dean Winchester ended up standing outside of his younger brother’s college lecture hall, his ass half frozen against the brick wall of the building, with only a large Mocha Expresso and an excuse that his baby brother needed some caffeine, and being shielded from the cold by his desire to see Castiel outside of his work, and to also see what happened when those big blue eyes widened to the size of golf balls when he saw how good Dean looked in skin-tight jeans. Also, there may be a few attractive young women their to witness (and observe Dean's unmatched good looks) so that just added to Dean's longing to go into Sam's fancy-ass college classroom that he was never able to go to (that made Dean stiffen, as he was still not fully over the whole idea of him not being a college graduate, but instead a barista who had to flirt with customers to get tips that could pay for the various expenses that apartments had).

**Notes for the Chapter:**

> Hey guys! Hope you enjoy the fic! Please leave comments and kudos to let me know. I'll be updating every week on Tuesdays! Also, if you have any suggestions/ constructive criticism, please leave it in the form of a comment; i am open to any and all suggestions!


	4. Dean Winchester only whistles when provoked

**Summary for the Chapter:**

> Dean shivered slightly, wrapping his leather jacket tighter around his shuddering body while he cursed Sam and winter and how attractive Castiel was. His fingers were going numb from the cold November chill, and his feet were frozen in the beat up doc martens he had bought several years back while he was in his “gothic” phase, and when he was trying to impress girls with that fact that his father wasn’t around and his nose had a metal bar through it.

**Notes for the Chapter:**

> Dean socializes with Sam's classmates, winks at Castiel, and skips home to the tune of "Strawberry fields" like in some mushy lovey-dovey musical from the '50s.

Dean shivered slightly, wrapping his leather jacket tighter around his shuddering body while he cursed Sam and winter and how attractive Castiel was. His fingers were going numb from the cold November chill, and his feet were frozen in the beat up doc martens he had bought several years back while he was in his “gothic” phase, and when he was trying to impress girls with that fact that his father wasn’t around and his nose had a metal bar through it.  
“Damn it, Moose, pick up your phone!” He growled into the mouth piece, only letting out a small chuckle at the Sam's nickname (which he hates), before shoving the beat up Blackberry into the back pocket of his jeans that he had somehow (miraculously) kept out of batter and coffee for the past 3 years. “Why the hell would you put a lecture hall in a separate building?” Dean groaned, taking a sidelong glance through the frost covered windows, barely able to make out Castiel (or Mr. Novak’s) slim figure due to the streetlights that weren’t actually working.  
Finally, ten curse-filled and angry minutes later, Sam popped his head out of the classroom’s thick wooden door and beckoned Dean inside. Awkwardly, Dean shuffled in after him, his boots leading snow inside as he huffed under his breath about the “Fucked up weather” and how “Sam needs to get his shit together”. Sam only chuckled at Dean’s sour attitude and led him across the room to the table where the students had brought in snacks for the 10 minute breaks they were allotted every hour during the test.  
“What did you bring, man?” A young Asian man with tussled black hair and a thick pair of glasses that framed a pair of almond brown eyes that were lined with dark bags (though it was a mystery how the glasses stayed on as long as they had) shoved past Sam, grabbing the first coffee he laid eyes on in Dean’s hands and raised his eyebrows at Sam before he nodded, then upturned the Styrofoam cup to his lips and hastily drank from it.  
“Good coffee,” He grinned, taking another gulp before turning to Dean and outstretching a hand that was covered in graphite staining, “I’m Kevin. Kevin Tran. I’m a Journalism major who was supposed to be a Doctor at MIT, and I haven’t slept in almost 32 hours ‘cause of this god damned test.” Dean shook his head, though it was weak and calloused, before clearing his throat and finally introducing himself. “Dean, Dean Winchester. Sammy’s older brother. Thought you guys could use some caffeine, and I, uh, work at a Coffee shop down town.”  
“Oh yeah, Supernatural, right? I’ve been there before, probably.” The cup of coffee- or, to be more exact, the first cup of coffee- was long gone, mixed in to the trash with pencil shavings and crumpled papers, and Kevin was eagerly grabbing another and proceeding to load it with a can of 5-hour energy he had stashed in his jean pockets.  
“Kevin, go easy on the coffee. You know what that shit can do to your system.” An older man with a thin upper lip and hair that kept slipping into his eyes remarked as he slapped Kevin on the back (poor Kevin almost toppled over at the force from it), laughing as the younger proceeded to chug the rest of the cup before turning and smacking the older on the arm.  
“These for us, eh Kev? Hot damn, we finally got somethin’ good!” The man’s eyes lit up at the sight of the table, fully stocked with Dean’s chocolate cookies and Styrofoam cups emblazed with the Supernatural Coffeehouse logo, and he grabbed one of each before finally noticing Dean.  
“Hey, man, I’m Gabriel. Economics major. And you are…..” He trailed off, studying Dean’s features with intense scrutiny before grabbing Dean’s hand and roughly shaking it, grinning slightly and showcasing a chipped tooth.  
“Dean, Dean Winchester. Sam’s older brother.” Hastily he wiped his hands on his jeans, as both men had hands covered in graphite and eraser dust, and it had then transferred to Dean.  
Dean suddenly felt very alone- almost like he was naked-, being in a sea of people who were obviously in the top of their class in both high school, and college. But, it had been Dean’s choice to drop out of community college (according to their father, John, Dean shouldn’t have even bothered going to college if he was only going to go to community) and it had also been Dean’s choice to not go back. Dean wasn’t like Sam; he was a slacker. He spent most of his high school days sneaking off campus to have a smoke or go down on whoever he was dating that week. He bummed homework off of his friends and cheated on any test he took. He barely even graduated high school; his record number of absences and detentions made it very hard to convince the female Principal to pass him without bribery.  
Sam, on the other hand, had a certain knack for school. Always at the top of his class, valedictorian every year in high school, captain of the math team, the spelling team, the physics team, ect. Sam had been the poster boy for all nerds. The only thing that made him stand out was when he had his growth spurt in the summer before junior year, and he sprouted up to 6 foot 4. He was the oddest looking kid on the math team, according to Dean, as he would come out to see Sam compete and swipe food from the different concession stands. So, college was the perfect fit for Sam once he graduated high school.  
“Damn good coffee, Dean, you know how to make it strong.” Gabriel grinned, taking another large swig before Sam grabbed the cup out of his hands and sniffed it accusingly.  
“Damn it, Gabriel, I told you, no more liquor! If Professor Novak found out, you’d be expelled- AGAIN.” Sam made an attempt to glare down at Gabriel, who only chuckled out of the side of his mouth before grabbing the cup again and taking a long gulp of it, until Sam snatched it right out of his hand and threw it into the trash can, where it landed with an audible thud and a faint sloshing noise.  
“Again?” Dean questioned, looking over at Sam and raising an eyebrow (a trick he had only recently grasped after Bobby showed him how to deal with rude customers).  
"I was kicked out of UMASS Amherst a couple years back ‘cause I brought in some spiked Mountain Dew and got the entire cheerleading squad pretty hammered before some big game. Administration got pretty pissed, and I barely spent any money getting in, so I flipped them off and got expelled.”  
"Just like that?” Dean questioned, staring at the man incredulously. I mean, at least Dean knew he wasn’t cut out for college. Maybe this guy just doesn’t get it.  
“Well, I didn’t really study… or get passing grades… or show up.” He chuckled nervously, like someone who is trying to make light of their failures, even though it is killing them inside.  
“Oh. I never went.” Dean shrugged, sipping his drink slowly and down casting his eyes to avoid the normal response. His life wasn’t great, but neither was anyone’s, and he could have been doing a lot worse that he was, so he never thought it was something to make people laugh. Apparently, many people took it as a joke, like he was asking to be a bagger at Wal-Mart or a cashier at McDonalds for the rest of his life. It was his business if he didn’t want to attend college, and no one else could convince him differently.  
“Are you ever gonna go?” Kevin piped up, his voice not filled with humor and pity, but more of a general curiosity, which still made Dean a little nervous, possibly more so than those who pitied and laughed at him.  
“Maybe. At some point.” He shrugged noncommittally, taking a sip from his drink before clapping Sam on the back. “It’s been nice, Sammy, nice meeting your friends and all, but I should get going.”  
Sam nodded, “Yeah, alright. See you around later, once your shift ends.” He smiled, and both Gabriel and Kevin waved to him as he walked out, only disappointed for a minute that he hadn’t seen Castiel, until he bumped right into him.  
“Dean!” He jumped slightly, his eyes widening, before he contained himself and awkwardly coughed, shifting his tie in his hands and fiddling with the handle of his briefcase, “Hello, Dean.”  
“Hey Cas.” He smiled softly, shuffling his feet awkwardly as he suddenly realized he had absolutely no idea what to say to this man outside of his coffee-shop.  
“Cas?” Castiel quirked his head to the side, smiling slightly as his eyes stared right into Dean’s.  
Dean cleared his throat, scratching the back of his neck sheepishly as he was unsure whether or not the nickname offended Castiel in some way.  
“Well, Dean, it was nice seeing you again, but I should go and, um….” Castiel coughed again, his brow furrowed as he searched for a word.  
“Teach?” Dean offered.  
“Teach! Yes, I should go… do that.” Despite his words, Castiel seemed very reluctant to tear himself away from Dean’s presence, even though there conversations had mostly been held through subtle glances and awkward coughing.  
“Bye Cas.” Dean waved flirtatiously, watching Castiel go the color of a fire hydrant before he coughed timidly and waved back.  
“Bye Dean. I’ll see you around… I’ll probably need something to eat later.” Now it was Castiel’s turn to flirt and wink, and in all honesty, Dean very much enjoyed it.  
Maybe he enjoyed it a bit too much for someone who supposedly didn’t believe in true love, not that it mattered to Dean anyways as he practically skipped home, so excited to see “Cas” later that he even (horribly) whistled the tune to “Strawberry Fields” by the Beatles.  
And Dean never whistled.  
Apparently unless Cas was involved.

**Notes for the Chapter:**

> Sorry i haven't posted in awhile. I've been busy with camp and stuff. Here's some adorable Dean and Cas and clueless Sam.

**Author's Note:**

> Hey guys! Hope you enjoy the fic! Please leave comments and kudos to let me know. I'll be updating every week on Tuesdays! Also, if you have any suggestions/ constructive criticism, please leave it in the form of a comment; i am open to any and all suggestions!


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